A nostalgic, buttery cake crowned with caramelized pineapple and bright maraschino cherries, enriched by browned butter and a whisper of cinnamon for a tropical-caramel finish.
Melt 1/3 cup salted butter in a small saucepan over medium heat for the topping; cook, stirring, until foamy and golden with a nutty aroma, 4–5 minutes, then immediately pour into a 9½-inch round pie plate or cake pan.
Stir a pinch of cinnamon into the brown sugar and sprinkle evenly over the browned butter in the pan.
Lift pineapple slices from the can, drain well, and pat dry. Arrange one slice in the center and six around it in a single layer. Halve three additional rings and stand the halves upright around the sides of the pan. Reserve 1/3 cup pineapple juice for the batter.
Place a maraschino cherry in the center of each pineapple ring and in any gaps. Refrigerate the pan while making the batter. Preheat oven to 350°F (175°C).
In a small bowl, whisk together cake flour, baking powder, and salt; set aside.
In a separate bowl, whisk melted butter (for batter), sugar, and eggs until well combined. Whisk in vanilla, sour cream, and the reserved pineapple juice until smooth.
Add the dry ingredients to the wet and whisk just until the batter is smooth with no dry streaks; do not overmix.
Remove the prepared pan from the fridge and pour the batter evenly over the pineapple and cherries.
Bake for 45 minutes, or until golden and a toothpick inserted in the center comes out clean. Cool in the pan for 30–45 minutes.
Invert onto a serving plate. Slice and serve, optionally with whipped cream or vanilla ice cream.